YHM - ORD

C$ 335 Find Cheap Flights from Hamilton to Chicago – Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hamilton to Chicago departing on 14/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
C$ 615
Multiple Airlines
Thu 10/9Sun 13/9
YHM - ORD • 3 stops
Cheapest one-way flights
C$ 335
WestJet
Wed 14/10
YHM - ORD • 1 stop
Direct flights
Not available
There are currently no direct flights between Hamilton and Chicago. You’ll need at least 1 connection.
Insights
Insights
Insights
Insights
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Hamilton to Chicago (YHM-ORD)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Hamilton to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Hamilton to Chicago

Thu, 10 Sep - Sun, 13 Sep
Multiple Airlines Logo
6:05 a.m. - 4:40 p.m.
YHM
-
ORD
35h 35m
3 stops
Multiple Airlines Logo
5:30 p.m. - 5:35 p.m.
ORD
-
YHM
23h 05m
3 stops
C$ 615Multiple Airlines
Thu, 3 Sep - Sun, 6 Sep
Multiple Airlines Logo
6:05 a.m. - 4:40 p.m.
YHM
-
ORD
35h 35m
3 stops
Multiple Airlines Logo
5:30 p.m. - 8:25 p.m.
ORD
-
YHM
25h 55m
3 stops
C$ 701Multiple Airlines
Thu, 3 Sep - Mon, 7 Sep
WestJet Logo
6:10 p.m. - 4:40 p.m.
YHM
-
ORD
23h 30m
1 stop
WestJet Logo
5:30 p.m. - 5:15 p.m.
ORD
-
YHM
22h 45m
1 stop
C$ 744WestJet
Fri, 4 Sep - Mon, 7 Sep
WestJet Logo
6:10 p.m. - 4:40 p.m.
YHM
-
ORD
23h 30m
1 stop
WestJet Logo
5:30 p.m. - 5:15 p.m.
ORD
-
YHM
22h 45m
1 stop
C$ 744WestJet
Thu, 3 Sep - Mon, 7 Sep
WestJet Logo
6:10 p.m. - 4:40 p.m.
YHM
-
ORD
23h 30m
1 stop
WestJet Logo
5:30 p.m. - 5:15 p.m.
ORD
-
YHM
22h 45m
1 stop
C$ 746WestJet
Thu, 10 Sep - Sun, 13 Sep
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.
YHM
-
ORD
34h 40m
2 stops
Multiple Airlines Logo
5:30 p.m. - 5:35 p.m.
ORD
-
YHM
23h 05m
3 stops
C$ 756Multiple Airlines
Thu, 10 Sep - Sun, 13 Sep
Multiple Airlines Logo
6:05 a.m. - 4:40 p.m.
YHM
-
ORD
35h 35m
3 stops
Multiple Airlines Logo
5:30 p.m. - 5:35 p.m.
ORD
-
YHM
23h 05m
3 stops
C$ 756Multiple Airlines
Sat, 5 Sep - Tue, 8 Sep
Multiple Airlines Logo
6:05 a.m. - 4:40 p.m.
YHM
-
ORD
35h 35m
3 stops
Multiple Airlines Logo
5:30 p.m. - 5:35 p.m.
ORD
-
YHM
23h 05m
3 stops
C$ 761Multiple Airlines
Fri, 4 Sep - Mon, 7 Sep
WestJet Logo
6:10 p.m. - 4:40 p.m.
YHM
-
ORD
23h 30m
1 stop
WestJet Logo
5:30 p.m. - 5:15 p.m.
ORD
-
YHM
22h 45m
1 stop
C$ 768WestJet
Sat, 5 Sep - Tue, 8 Sep
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.
YHM
-
ORD
34h 40m
2 stops
Multiple Airlines Logo
5:30 p.m. - 5:35 p.m.
ORD
-
YHM
23h 05m
3 stops
C$ 771Multiple Airlines
Booking Insights

KAYAK's insights & trends for Hamilton to Chicago flights

Get data-powered insights and trends into flights from Hamilton to Chicago to help you find the cheapest flights, the best time to fly and much more.

How long does a flight from Hamilton to Chicago take?

There are no direct flights for this route listed on KAYAK. The shortest multi-flight duration is 3h 15m.

Find deals

Good to know

Cheapest flight

C$ 335
Flight from Hamilton to Chicago

When to book flights from Hamilton to Chicago

Are your dates flexible? Find out the best times to travel from Hamilton to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Hamilton to Chicago flights

  • What is the cheapest flight from Hamilton to Chicago O'Hare Intl Airport?

    In the last 5 days, the lowest price for a flight from Hamilton to Chicago O'Hare Intl Airport was C$ 335 for a one-way ticket and C$ 615 for a round-trip.

  • Which airports will I be using when flying from Hamilton to Chicago?

    Hamilton airport is called Hamilton and the only airport in Chicago is Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Hamilton to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Hamilton to Chicago?

    Star Alliance is the only airline alliance operating flights between Hamilton and Chicago.

  • How does KAYAK find such low prices on flights from Hamilton to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hamilton to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hamilton to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hamilton is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Hamilton to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hamilton with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hamilton to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hamilton up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Hamilton to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Hamilton to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Hamilton to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
Air CanadaOverall score based on 11415 reviews
7.1Comfort
7.8Crew
7.3Boarding
6.8Entertainment
6.3Food
Airline reviews

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

2.0 MediocreAnonymous, Nov 2025
YYZ - ORD
Read more Air Canada reviews

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

flight was delayed 6 hours for weather, then cancelled because of the crash in toronto, but none of the links to cancel or rebook my flights are working

They charge 5 dollars for plastic headphones for a flight of 1 hour! Seats are awful. Service is terrible.

Everything was seamless. I would have appreciated knowing there would not be any real food available for purchase in advance. Otherwise a great experience. Thank you!

I was mostly pleased. My greatest disappointment was with respect to the timely update to the estimated departure and arrival times. It was especially sad that the arrival time was not updated online once we were in flight so as to allow my wife to arrive on time to the airport. She was not happy.

Seats weren't comfortable, could have used more let room

Flight was delayed more than 120 min. I had carry on bag but the airplane was full and they had to get it checked in. I had to wait for the small carry on bag at the airport carousel

Flight was delayed 3 hrs, one of the flt attendants was rude to me & I was forced to pay for a middle seat.

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

Everything you need to know for your flight from Hamilton to Chicago

Information on your arrival and departure airports

Hamilton (YHM)
O'Hare Intl (ORD)